Hpa-an is a small town (pop.~40,000) in Kayin State in Southeastern Myanmar
"Bus" (meaning covered pick-up truck crammed with way too many people) from Kyaiktito is about 4 hours, 5,000 Kyat. You will probably need to change pickup in Thaton but that is included in the price. It might be marginally cheaper to take the regular pickup from Kyaiktito to the train station (500 kt), then go to the main road and wave down any of the pickups going towards Thaton, Mawlamyine, or Hpa An. Air conditioned buses, at 12 noon and 3 pm, from Kyaiktiyo to Hpa An (those are coming from Yangon) take around 4 hours and about 7,000 kyat; unlike with the pickup that departs from the "base camp"(Kinpun), with the bus you have to take another transportation from Kinpun down to the bigger town on the highway to meet the bus. If you book your ticket at the guesthouse in Kinpun, the owner's son or other relative might give you a ride on the back of their motorcycle to the main road to meet the bus.
Yangon - Buses run several times a day. the trip takes about 6 hrs. 10,000 kyat. To go back from Hpa An to Yangon buses can be easily found for 5000 kt.
Mawlamyine almost hourly morning departure bus takes 2 hours, 1,000 kyat local bus to 7,500 Kyat AC Van. It is possible to catch passing one beside clock tower/CB Bank. Private boat can be arranged through your guesthouse.
Myawaddy to Mae Sot, Thailand. Several departures in the morning, 10,000 Kyat. You may find shared taxi (10,000 to 20,000) or hiring a car (50,000 kyat), much more comfortable and SAFE on this narrow mountainous road.. The route is alternate day one-way.
The popular government ferry ("slow boat") from Mawlalmyine to Hpa-An was discontinued as of about December 2012. A fast boat is sometimes available, arranged through the guesthouses in Mawlamyine (70,000 kyat to charter a private boat from Mawlamyine to Hpa-an). Breeze GH organizes a daily boat leaving at 8:15AM for 10000 per person (March 2014), sign up the day before.
Motorbikes can be rented from Soe Brother's Guesthouse for 8,000 kyat/day. They also give you a map. Bicycles go for 2000 kt for a day or 1000 kt for half a day. There are pickups that go to some of the sites around Hpa An. Tuktuks usually charge 1000 per person between jetty, bus station and hotels.
Shweyinhmyaw Paya, the pagoda on the northwest end of town has nice views of the sunset; you can watch from a viewing tower or at the side of the river next to the pagoda. There is a ferry below the pagoda for Mt. Hpar Pu on the other side.
Small lake in the southern part of the city, nice for a late evening stroll & a nice view from Mt Zwegabin across a wooden bridge.
The traditional market, just downhill from Soe Brothers guesthouse and across from the red mosque, is where you can hear the Karen/Kayin language spoken and a good spot for food in the morning. The two indoor buildings have housewares, shampoo, mosquito repellent, etc. on the ground floor and clothing and fabrics on the second floors. There is a fruit market outside and a small gold market (beware artificial gems!) around the perimeter. Good value is the hand woven longi fabric in traditional Karen ikat patterns (2000 to 6000 kyats, depending on size, and whether cotton or synthetic "seelon").
If you buy longi material, and you can't keep the thing from falling off the way the locals do, you may want to have it made up at a tailor with discreet ties or zippers. A good tailor shop is, from the clock tower, take the street next to the bus ticket office, and go uphill towards the monastery. The road curves around to the right, then turn right and you will see the treadle sewing machines in a shop on your right. You can also take the road up from the triangular roundabout, walk uphill past the New Day bakery shop, then turn left at the first intersection. It's on your left, maybe the second building. If you need to travel quickly, they can expedite it for an additional fee.
Traditional massage, head and shoulders and/or feet. Also pedicure, with nail polish (about 2000 kyats), including original multicolor freehand designs (for around 5000 kyats June 2013). From the clock tower, take the road by the bus ticket office towards the monastery. It is the third house on the left, the sign says beauty salon.
Not much to do in the city itself, but beautiful surroundings outside of the city. You can arrange an all-day tour at the Soe Brothers Guesthouse or at Golden Sky Guesthouse (see below for details) - they'll take you out in the countryside, to visit different caves (at one you can swim in a small natural pool) and the Kyauk Kalap Monastery in the middle of a small lake. Really nice day.
You can also explore by yourself, renting a bicycle (some places are no further than 5km) or motorbike, or catching pick ups from the market & walking around.
You can also take a boat across the river to a mountain (???).
Another possibility is to climb Mt Zwegabin late afternoon (2.5hours, many steps), sleep in the small monastery at the top (bamboo mat on the floor, PLEASE BE QUIET AND RESPECT THE MONKS' HOSPITALITY) and climb down the next morning (1.5 hours) after watching sunrise over the gorgeous views all around. The top can be accessed from the west or the east, the latter being steeper. As of March 2014 there are numerous reports that the monks are not very hospitable. It seems that the immigration prohibit monks to host any foreigner overnight at the monastery report from May 2014. If you decide to sleep on the top bare in mind that you might be asked to leave by sunset, bring flashlights with you to come down in case it's dark. On the other hand, if you can spend the night be very polite, give a donation (!) and dress appropriately, despite the heat. Otherwise, it is possible to climb the mountain early in the morning or late in the evening, going there, respectively returning, in the dark, so as to avoid the midday heat. The west side access is more popular and it has a monastery with hundreds of Buddha statues at the bottom. This is around 10 km from Hpa An (perfectly doable on a bicycle). The trails are well marked on OpenStreetMap.
All run about 500 kyat per hour (May 2013)
Ask Soe Brothers GH or Than Lwan O GH for a map & recommendations.
Lucky, a block from the market, has frosted mugs and ice cold bottles of Tiger, also Myanmar on tap, and a generator for power fails, and stays open later than most, not to mention the great pork fried noodles. This is convenient if you are staying at Soe Brothers; in case of power fail or rainstorm, it is a short walk back in the pitch dark.